4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchids Gastrodia elata,[4] Galeola faberi,[5] and the Vanilla orchids.

4-Hydroxybenzaldehyde
Names
Preferred IUPAC name
4-Hydroxybenzaldehyde
Other names
p-Hydroxybenzaldehyde, 4-formylphenol[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.182
KEGG
UNII
  • InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H checkY
    Key: RGHHSNMVTDWUBI-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
    Key: RGHHSNMVTDWUBI-UHFFFAOYAN
  • O=Cc1ccc(O)cc1
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Appearance yellow to tan powder
Density 1.129 g/cm3 (130 °C)[1]
Melting point 116 °C (241 °F; 389 K)[1]
Boiling point 310 to 311 °C (590 to 592 °F; 583 to 584 K)
12.9 g/L[2]
Acidity (pKa) 7.61 (25 °C)[3]
-78.0·10−6 cm3/mol
1.57051 (130 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Chemistry

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidized, and the hydrogen peroxide is reduced.

Derivatives

Metabolism

p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).[6]

See also

References

  1. Haynes, p. 3.304
  2. Haynes, p. 5.154
  3. Haynes, p. 5.92
  4. Ha, J. H.; Lee, D. U.; Lee, J. T.; Kim, J. S.; Yong, C. S.; Kim, J. A.; Ha, J. S.; Huh, K. (2000). "4-Hydroxybenzaldehyde from Gastrodia elata B1. Is active in the antioxidation and GABAergic neuromodulation of the rat brain". Journal of Ethnopharmacology. 73 (1–2): 329–333. doi:10.1016/S0378-8741(00)00313-5. PMID 11025174.
  5. Li, Y. M.; Zhou, Z. L.; Hong, Y. F. (1993). "(title in Chinese)" [Studies on the phenolic derivatives from Galeola faberi Rolfe]. Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 28 (10): 766–771. PMID 8009989.
  6. Sircar, D.; Mitra, A. (2008). "Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota". Journal of Plant Physiology. 165 (4): 407–414. doi:10.1016/j.jplph.2007.05.005. PMID 17658659.

Cited sources

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